


Cocksure

by Wayward_and_Worn



Category: Supernatural
Genre: F/M, Teasing, Vaginal Sex
Language: English
Status: Completed
Published: 2019-01-07
Updated: 2019-01-07
Packaged: 2019-10-05 21:53:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,272
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17333030
Author URL: https://archiveofourown.org/users/Wayward_and_Worn/pseuds/Wayward_and_Worn
Summary: Being a hunter and on the road a lot, you need to find ways to pass the time between all those miles.





	Cocksure

**Author's Note:**

> Three way relationship is established.

                 Another one of the million ways to kill time on the long haul trips from case to case.  Cocksure, as they called it, started off with someone, probably Dean, running their mouth.  Something like, “You’d be begging for me to be balls deep in less than a minute.”

                Challenge accepted.

                From the first time, the game evolved quickly.  Rules were simple.  Just the tip.  And no unfair touching.  Words only.  First one to slide the cock home lost.  Begging counts as words.  If you come, you automatically lose.  There was no time limit. 

                The real fun began when Sam challenged her to Cocksure while in the Impala.  With Dean driving. 

                “Hell no!”  Dean declared as they jumped on the highway from the most recent diner dinner.  The sun was setting quickly as they drove towards home.  They wanted to see how far they could get in a 9 hour drive before stopping.  Dean was hoping to make it straight to the bunker.  They were already three hours in.   

                “Why not?”  Sam challenged, “You played in here in Madison!”

                “Yeah, but she was parked and I didn’t make you watch!”  Dean retorted.

                “Envy?”  Y/N had sat up to put her lips to Dean’s ear, wrapping her arms around his shoulders.  He brought one hand up to hold both of hers.  Pulling them up to his mouth and kissed her bruised knuckles.  “Yes,” he grumbled.

                She turned to Sam with a smile, “It IS his car.”

                Sam’s eyes widened and he pointed at her.  “You KNOW you can’t do it!”  He accused.  “That’s why you’re siding with Dean now.”

                “You’re just being silly.”  She said softly.  “You’re probably already hard and don’t know what to do with yourself.”  She sighed into Dean’s ear and held him tightly. 

                Sam turned his eyes back to the road with a huff.  “I totally would have won.”  He pouted.

                “I guess we’ll never know.”  She singsonged, running her hands down Dean’s chest.

                “Wait a second, am I being played?”  Dean suddenly blurted.  “Y/N, did you side with me just so I’d say no?”  He half turned to try to look at her in the back. 

                “Dean!”  She gasped in shock.  It was total bullshit shock, and she was trying to hide the fact that she was blushing.  “Of course not!”  She pressed her forehead to the back of Dean’s hair and tried to lock her hands around his neck but he leaned forward and broke out of her reach. 

                “You have never turned down a challenge.”  Dean met her eyes in the mirror and she quickly looked away.  “Sammy, you get your giant ass back there and defend the Winchester name!”

                Sam turned sideways again to watch her.  She was sitting with her head down, scowling at her hands.  “Hey, if you decline, it’s—“

                Her head snapped up and her eyes burned with defiance.  “Get back here so you can beg me to let you in.”  She hissed.

                Sam flipped over into the backseat with unsettling grace for a 6’4” hunter.  Dean was just grateful he didn’t kick out a window, or punch him in the face. 

                Clothes were shed quickly and before long, Y/N was straddling the younger Winchester’s lap, pressing his erection between them.  As she was trailing her lips down Sam’s neck, causing him to pulse with need, he caught his brother’s eyes in the rearview mirror.  “Enjoying the view, Big Brother?’  He hissed as she sucked a new mark at his collarbone.  “You’ll pay for that one.”  He said into her ear, nipping the lobe. 

                Dean raised an eyebrow.  Barely noticeable in the dim light.  Darkness had fully fallen now and the only continuous light came from the glow of the dashboard.  The passing streetlights keeping time as they sped away from the city.  “I’ll take what I can get.  Unless you want to turn her around.”  He responded dryly.

                Sam and Y/N looked at each other, for a moment and then both nodded.  She leaned in for a deep kiss before rising up, and with Sam’s assistance, turned to face forward.  Sam’s weeping erection was now pressed up against his stomach and her ass.  She rocked a little, the pressure causing Sam to moan softly. 

                “That’s more like it.”  Dean said appreciatively. 

                Y/N reached her hands up, flattening her palms against the car ceiling while Sam’s hands ran up her sides, around to her stomach, and up to cup both breasts.  She moaned softly, arching her body and letting her head fall back over his shoulder.  Tweaking and twisting her nipples, Sam’s name fell from her lips.  Dean blinked slowly, trying to keep his eyes on the road and on her as much as possible without killing them all.  His hard-on was already making itself known.

                Sliding one hand down between her split thighs, Sam caressed her swollen nerves.  She yelped and rotated her hips against him.  “I think we’re ready.”  She gasped, opening her eyes to see Dean’s burning into hers from the rearview.  He winked.  “Can I stay facing forward?”  She half turned to face Sam. 

                He shrugged, pushing two fingers into her and pumping a couple of times.  “If you like.”  He grasped her hips and helped lift her up.  In this position she was able to brace her feet on the floor, almost standing to hold over Sam’s cock.  He positioned under her and she moaned sinfully as the head slipped inside.  She let her head drop forward, gripping the seat in front of her as she fought to drop down and bring this to an immediate end.  “Go.”  He said thickly.

                As soon as his hands fell from her hips, she knew she was in trouble.  She had initially been concerned about Dean’s presence in the car; an unfair advantage as the sexual tension was so much worse with both of them around.  Another problem she had not foreseen was in Baby herself.  Being in the car was one thing.  Being in the car while in motion, the vibration of the engine and the treads on the road sent low, thrumming tremors straight through Sam’s cock, over her folds and directly to her clit.  This might be a short contest after all. 

                But Sam was feeling it too.  The tremors, focused at his cockhead where he was enveloped in her warmth, “Oh god, I just want to pull you down and hold you there.”  Sam growled.  “Can you feel that?!”

                “Mmmhmm.”  She purred, “Why don’t you then?  Do it and put us out of our misery so we can do what we really want to do.”  She returned her eyes to the rearview and met Dean’s again.  “Grab my hips and just pull me onto that perfect cock.”  She watched in satisfaction as his eyes half rolled back into his head before returning to the road. 

                “Just slide on.”  Sam countered.  “Come on, you didn’t really want to do this anyways.  Open those perfect legs and let me slip in.  We can play this anytime.”  She felt him adjust his legs a little, trying to make himself more stable in the motion of the car.  It didn’t really work.   

                “Sam,” she whined, “Don’t you want to pull my hair?  Don’t you want to pound into me and make me scream your name?”

                “Yes,” he breathed.  The sound of the highway almost carrying the answer away from them. 

                “I want you to, Sam.”  She purred again.  “I want your hands in my hair, I want you holding me down, forcing my lips open and pushing that fucking cock all the way in.”  She felt him tremble beneath her, she could imagine him clenching his fists.

                “Which lips?”  Dean whispered huskily.  He met her eyes again, the darkness of the world outside giving his eyes no color but a shine from the dashboard.  It was very reminiscent of Demon Dean’s eyes.  An extra pulse of heat caressed her skin. 

                She flicked her tongue out over her bottom lip, “Dealer’s choice.”  She whispered.

                “Just drop down, baby,” Sam’s voice was now dark and forced.  He was losing.  She could tell.  “Just let me in and it’s all yours.”  A grunt escaped him.  “I’ll make you come in so many ways.”  He promised. 

                “Oh?”  She closed her eyes.  Her bottom lip caught between her teeth.

                “Yes.  My tongue, my fingers, however you want.  All night.”

                She moaned louder in response.  The vibrations became more pronounced as the car met a rougher, older, highway surface.  “Do you want to make me scream?”

                “I always want that.”  He growled as she glanced to her right.  She smiled in a small victory, he was definitely clenching his fists, fighting to keep them from grabbing her.  All she needed was the right words.  The right words to drive him over the edge and claim her larger victory.   

                She started gasping again.  Sam’s name on her lips in small cries that echoed in the confines of the car.  Her head fell forward, resting on the seat back.  “Please.”  She whined. 

                “Sam,” Dean barked, “If this doesn’t end soon, I’m pulling over and I’m gonna fuck her!”

                “Then we both lose,” she purred near Dean’s ear.  “Or maybe we’d win.  But it sure would feel good.”     

                “Is that what you want?”  Sam asked and she swore that he swelled beneath and within her.  “You want to take us both?”

                She froze and cursed at her failed verbal filter.  Taking this detour through her super-secret fantasy was not planned.  She often dreamed of a threesome but never ever dared to—“

                “You do!”  Sam’s voice broke through her inner monologue.  He groaned and when he spoke again, it was through gritted teeth.  “I can feel you, you’re hotter and wetter now.  You want us both.”

                She was in serious trouble.  Sam’s voice, Dean’s eyes, the vibrations, and her secret accidentally let out was about to push her over the edge and right onto Sam.

                “How do you want us?”  Sam demanded.

                “Sam, please.” She begged.

                “Do you want me to hold you open while my big brother fucks you?”

                She let out a string of gibberish.  Mostly vowels.  Her legs began to shake.

                “Or do you want his cock in your mouth and mine balls deep in that sweet, tight, pussy?”  He pulsed, fighting the urge to flex his erection against her straining walls. 

                She found Dean’s eyes once again, the white-hot desire couldn’t be hidden in the darkness.  His need burned right through her resolve.

                “Sam.”  Her voice was pleading.

                Sam leaned forward, not enough to press his chest to her back but enough for his voice to reach her ear, “You can have it.”  He said.  “All of it.”

                That was it.  She slapped her hand down on Dean’s shoulder, shifted and fully impaled herself on Sam.  They both shouted in relief and ecstasy.  She felt Dean release a pent up breath as Sam wrapped one arm around her waist, twisted his other in her hair.  She hissed in pleasure, “Please, you win.”  The full feeling and the vibrations sent rippling waves of fire through her body.  He yanked her head up so she was facing forward.

                “Look at him.  Look at him while you get fucked.”  Noticing that his knuckles were white on the wheel, she held Dean’s eyes as much as she could.  She moaned in bliss when Sam’s hand came up and harshly tweaked one of her nipples.  “Ride.”  He growled, thrusting his hips up into her.  Bracing her legs, she bounced up and down on his cock, as he demanded.  Pleasure building up quickly, she gripped Dean’s shoulder hard. 

                “Sam,” she moaned, “I won’t last.”  She mewed, her eyes still fixed on his brother.  “You, we, this feels so fucking good.”

                “Should we stop?” He panted, gripping her hips and bringing her to a slow ride.  Her core pulsed in protest. 

                “Noooo.” She closed her eyes and fell back against his sweat-slicked chest, her head resting on his shoulder.  He turned and bit gently into the side of her neck, his tongue caressing the sensitive flesh.  She wailed, moving one hand to massage her clit. 

                “Say “please.””  He whispered, nipping her ear. 

                “Please.”  She immediately responded.  “Sam, please, make me come.”

                The arm around her waist tightened.  He thrust his hand back into her hair, pushing her forward harshly.  Her breasts squashed against the back of the seat.  “Eyes on Dean.”  Then began furiously pumping into her.  Yelping with each thrust, she tried to focus.  He growled behind her, his hand dipping lower to swirl around her aching clit.  “Come.”  He demanded.

                She couldn’t keep up.  She closed her eyes, let her head fall forward and wailed his name.  Her orgasm hitting causing her whole body to tense, muscle walls clenching around Sam’s cock, pushing him over the edge into his own orgasm. 

                Their cries faded, and Y/N went limp, her head resting on the seat back.  She finally unlocked her fingers from Dean’s shoulder.  Neither of them noticing that Dean had exited the highway and was speeding towards a hotel. 

                “What’s going on?”  Sam asked, in breathless confusion. 

                “We’re stopping.”  Dean said gruffly.  They were still more than four hours from the bunker. 

                “I thought you wanted to get home.”  She panted, raising her head to study the approaching town.  She shifted a little and grunted as Sam slipped out of her warmth. 

                “I’m fairly certain you left holes in my shoulder and I’ve been steering with my dick for the last 20 miles.  We’re stopping.  I need relief.”

                “Yes sir.”  She responded with a sly smile.  


End file.
